TWI443180B - Chiral binaphthyl compounds - Google Patents
Chiral binaphthyl compounds Download PDFInfo
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- TWI443180B TWI443180B TW099145587A TW99145587A TWI443180B TW I443180 B TWI443180 B TW I443180B TW 099145587 A TW099145587 A TW 099145587A TW 99145587 A TW99145587 A TW 99145587A TW I443180 B TWI443180 B TW I443180B
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- liquid crystal
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- naphthyl
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 title 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- MNRCSHSTIWDUPJ-VXKWHMMOSA-N (1s,2s)-1,2-dinaphthalen-1-ylethane-1,2-diol Chemical compound C1=CC=C2C([C@@H]([C@@H](O)C=3C4=CC=CC=C4C=CC=3)O)=CC=CC2=C1 MNRCSHSTIWDUPJ-VXKWHMMOSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- -1 trans-4-pentylcyclohexylbenzoic acid (4-(trans-4-pentylcyclohexyl)benzoic acid) Chemical compound 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本發明是有關於一種旋光化合物，且特別是有關於一種應用於液晶的對掌性雙萘基旋光化合物。This invention relates to an optically active compound, and more particularly to a palmitic bis-naphthyl optically active compound for use in liquid crystals.
現今業界廣泛應用的液晶顯示器種類繁多，依其內含之液晶分子及顯像原理的不同可大致分為向列型(Nematic)液晶的顯示元件、扭轉90度的扭轉向列型(Twisted Nematic，TN)液晶顯示元件、扭轉180度或180度以上的超扭轉向列型(Super Twisted Nematic；STN)液晶顯示元件、表面穩定膽固醇型結構(Surface-Stabilized Cholesteric Texture；SSCT)液晶顯示元件、聚合物穩定膽固醇型結構(polymer-stabilized cholesteric texture；PSCT)型液晶板或薄膜電晶體(TFT)型液晶顯示元件。A wide variety of liquid crystal displays widely used in the industry today can be roughly classified into Nematic liquid crystal display elements and twisted nematic twisted nematic (Twisted Nematic) according to the liquid crystal molecules and imaging principles contained therein. TN) liquid crystal display element, super twisted nematic (STN) liquid crystal display element twisted by 180 degrees or more, surface-stabilized Cholesteric Texture (SSCT) liquid crystal display element, polymer A polymer-stabilized cholesteric texture (PSCT) type liquid crystal panel or a thin film transistor (TFT) type liquid crystal display element.
液晶顯示元件的顯示品質乃是其核心價值，而液晶顯示元件的顯示品質可由數項重要特性來評估，例如：電壓保持率(Voltage Holding Ratio;VHR)及殘留直流電數值等。若電壓保持率較低，那麼在圖框時間(frame time)中施加至液晶的電壓會下降，結果會導致亮度下降，甚至會阻礙正常的灰階顯示。另一方面，如果殘留直流電較大，那麼有時會產生所謂的”殘影”，即施加電壓後無論斷電與否，都殘留應消失的圖像。The display quality of a liquid crystal display element is its core value, and the display quality of a liquid crystal display element can be evaluated by several important characteristics, such as a voltage holding ratio (VHR) and a residual direct current value. If the voltage holding ratio is low, the voltage applied to the liquid crystal during frame time will decrease, resulting in a decrease in brightness and even hindering normal gray scale display. On the other hand, if the residual direct current is large, a so-called "afterimage" may occur, that is, an image that should disappear regardless of whether the power is turned off or not after the voltage is applied.
本發明係關於一種應用於液晶的對掌性雙萘基旋光化合物，擁有良好溶解性與相當高的螺旋扭轉力(Helical Twisting Power;HTP)。此系列旋光性化合物適用於各類顯示器的液晶配方，依不同比例與液晶調配後，提供高電壓保持率(Voltage Holding Ratio;VHR)，可幫助降低影像殘留並提高畫面對比。The present invention relates to a palmitic bis-naphthyl optically active compound applied to a liquid crystal, which has good solubility and a relatively high helical torsion force (HTP). This series of optically active compounds are suitable for liquid crystal formulations of various types of displays. They are supplied with a high voltage holding ratio (VHR) after being blended with liquid crystals in different proportions to help reduce image sticking and improve image contrast.
本發明提供一種對掌性雙萘基化合物，具下列化學式(I)結構：The present invention provides a palmitic bis-naphthyl compound having the following chemical formula (I):
其中，Y為重複單元以-(A1 -Z)m-A2 -表示，A1 與A2 為環狀結構，可分別選自於下列族群包括：Wherein Y is a repeating unit represented by -(A 1 -Z)mA 2 -, and A 1 and A 2 are cyclic structures, which are respectively selected from the following groups:
X與Z為相同或不同的連接基(linking group)可分別選自於下列族群包括─O─,─S─,─CO─,─COO─,─OCO─,─O─COO─,─CO─N(R1 )─,─N(R1 )─CO─,─OCH2 ─,─CH2 O─,─SCH2 ─,─CH2 S─,─CF2 O─,─OCF2 ─,─CF2 S─,─SCF2 ─,─CH2 CH2 ─,─CF2 CH2 ─,─CH2 CF2 ─,─CF2 CF2 ─,─CH=CH─,─CF=CH─,─CH=CF─,─CF=CF─,─C≡C─,─CH=CH─COO─,─OCO─,─CH=CH─與一單鍵，a、b與c分別獨立為0、1或2，m為0、1、2或3，R為C1 ~C30 之直鏈或支鏈烷基、C1 ~C30 之直鏈或支鏈烷基且其中的單一或多個─CH2 ─係被─O─,─S─,─NH─,─N(CH3 )─,─CO─,─CO─O─,─O─CO─,─CH=CH─或─C≡C─所取代、或前述之烷基選擇性具有─F,─Cl,─Br,─NCS,─CN,─OCF3 之取代者。The linking groups in which X and Z are the same or different may be selected from the following groups, respectively: -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO -N(R 1 )-,-N(R 1 )-CO─,-OCH 2 ─,-CH 2 O-,─SCH 2 ─,-CH 2 S─,─CF 2 O─,─OCF 2 ─ , -CF 2 S-, -SCF 2 -, -CH 2 CH 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH=CH-, -CF=CH ─, ─CH=CF─, ─CF=CF─, ─C≡C─, ─CH=CH─COO─, ─OCO─, ─CH=CH- and a single key, a, b and c are independent 0, 1 or 2, m is 2 or 3, R is a straight-chain C 1 ~ C 30 of chain or branched alkyl, C 1 ~ C 30 straight-chain or branched alkyl group and the mono- or wherein A plurality of -CH 2 - are -O-, -S-, -NH-, -N(CH 3 )-, -CO-, -CO-O-, -O-CO-, -CH=CH- or -C≡C--Substituted, or the aforementioned alkyl selectivity has the substitution of -F, -Cl, -Br, -NCS, -CN, -OCF 3 .
根據本發明之實施例，本發明所述之對掌性雙萘基化合物可具下列化學式結構，其中R=C5 H11 According to an embodiment of the present invention, the palmitic bis-naphthyl compound of the present invention may have the following chemical formula, wherein R = C 5 H 11
。.
根據本發明之實施例，本發明所述之對掌性雙萘基化合物可具下列化學式結構，其中R=C7 H15 According to an embodiment of the present invention, the palmitic bis-naphthyl compound of the present invention may have the following chemical formula, wherein R = C 7 H 15
為讓本發明之上述特徵和優點能更明顯易懂，下文特舉實施例，並配合所附圖式作詳細說明如下。The above described features and advantages of the present invention will be more apparent from the following description.
本發明係關於一種對掌性雙萘基旋光化合物，擁有良好溶解性與相當高的螺旋扭轉力(HTP)。此系列旋光性化合物適用於各類顯示器的液晶配方，依不同比例作為液晶摻雜物與液晶調配後，使液晶面板具有高電壓維持比(Voltage Holding Ratio;VHR)，可幫助降低影像殘留並提高畫面對比。The present invention relates to a palmitic bis-naphthyl optically active compound having good solubility and a relatively high helical twisting force (HTP). This series of optically active compounds are suitable for liquid crystal formulations of various types of displays. When liquid crystal dopants are mixed with liquid crystals in different proportions, the liquid crystal panel has a high voltage holding ratio (VHR), which can help reduce image sticking and improve Picture contrast.
由於液晶分子的光學特性可經由摻雜質(dopant)的摻入而加以改善或修飾。本發明之對掌性雙萘基旋光化合物可作為液晶組成物之摻雜物。Since the optical properties of the liquid crystal molecules can be improved or modified via doping of dopants. The palmitic bis-naphthyl optically active compound of the present invention can be used as a dopant for a liquid crystal composition.
本發明所謂之「液晶」包括各種常見之液晶面板或液晶螢幕所用之液晶，其範圍包括向列型液晶或膽固醇液晶等。上述液晶組成材料之更替調整，應為此領域發明者所能理解，也是本發明所欲保護的範圍。The "liquid crystal" as used in the present invention includes liquid crystals used in various conventional liquid crystal panels or liquid crystal screens, and the range thereof includes nematic liquid crystal or cholesteric liquid crystal. The replacement of the liquid crystal composition materials described above should be understood by those skilled in the art and is also intended to be protected by the present invention.
本發明之對掌性雙萘基旋光化合物以下列通式(I)代表之：The palmitic bis-naphthyl optically active compound of the present invention is represented by the following general formula (I):
其中，Y為重複單元以-(A1 -Z)m-A2 -表示，A1 與A2 為環狀結構，可分別選自於下列族群包括：Wherein Y is a repeating unit represented by -(A 1 -Z)mA 2 -, and A 1 and A 2 are cyclic structures, which are respectively selected from the following groups:
X與Z為相同或不同的連接基(linking group)可分別選自於下列族群包括─O─,─S─,─CO─,─COO─,─OCO─,─O─COO─,─CO─N(R1 )─,─N(R1 )─CO─,─OCH2 ─,─CH2 O─,─SCH2 ─,─CH2 S─,─CF2 O─,─OCF2 ─,─CF2 S─,─SCF2 ─,─CH2 CH2 ─,─CF2 CH2 ─,─CH2 CF2 ─,─CF2 CF2 ─,─CH=CH─,─CF=CH─,─CH=CF─,─CF=CF─,─C≡C─,─CH=CH─COO─,─OCO─,─CH=CH─與一單鍵，其中a、b與c分別獨立為0、1或2，m為0、1、2或3，R為C1 ~C30 之直鏈或支鏈烷基、C1 ~C30 之直鏈或支鏈烷基且其中的單一或多個─CH2 ─係被─O─,─S─,─NH─,─N(CH3 )─,─CO─,─CO─O─,─O─CO─,─CH=CH─或─C≡C─所取代、或前述之烷基選擇性具有─F,─Cl,─Br,─NCS,─CN,─OCF3 之取代者。The linking groups in which X and Z are the same or different may be selected from the following groups, respectively: -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO -N(R 1 )-,-N(R 1 )-CO─,-OCH 2 ─,-CH 2 O-,─SCH 2 ─,-CH 2 S─,─CF 2 O─,─OCF 2 ─ , -CF 2 S-, -SCF 2 -, -CH 2 CH 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH=CH-, -CF=CH ─, ─CH=CF─, ─CF=CF─, ─C≡C─, ─CH=CH─COO─, ─OCO─, ─CH=CH- and a single key, where a, b and c are independent is 0, 1 or 2, m is 2 or 3, R is a straight-chain C 1 ~ C 30 of chain or branched alkyl, C 1 ~ C 30 straight-chain or branched alkyl group of single and wherein Or a plurality of -CH 2 - are -O-, -S-, -NH-, -N(CH 3 )-, -CO-, -CO-O-, -O-CO-, -CH=CH- Or -C≡C-substituted, or the aforementioned alkyl selectivity has a substitution of -F, -Cl, -Br, -NCS, -CN, -OCF 3 .
本發明之對掌性雙萘基旋光化合物可透過此領域已知之有機合成製程製備，並視不同取代基，而調整使用合成溶劑、反應條件、溫度或添加物等，該些詳細步驟或實施條件調整並不限於本說明書之實施例，而為此領域者所理解。The palmitic bis-naphthyl optically active compound of the present invention can be prepared by an organic synthesis process known in the art, and the synthetic solvent, reaction conditions, temperature or additives, etc., can be adjusted depending on the different substituents, and the detailed steps or implementation conditions. The adjustment is not limited to the embodiments of the present specification, but is understood by those skilled in the art.
將8 mmol的反式-4-戊基環己基苯甲酸(4-(trans-4-pentylcyclohexyl)benzoic acid)與20 ml無水四氫呋喃(dry THF)置於反應瓶中，待其溶解後加熱至迴流溫度。溫度到達後，加入12 mmol的1,1-羰基二咪唑(1,1'-Carbonyldiimidazole；CDI)，攪拌反應過夜，反應溶液由透明液體變為黃色液體。將反應冷卻至室溫，減壓濃縮將THF去除，得到黃色固體。以二氯甲烷與水萃取、取有機層，加入無水硫酸鎂除水後，減壓濃縮得中間產物白色酯類產物(a) 2.96 g(9.2 mmol)。8 mmol of trans-4-pentylcyclohexylbenzoic acid (4-(trans-4-pentylcyclohexyl)benzoic acid) and 20 ml of anhydrous tetrahydrofuran (dry THF) were placed in a reaction flask, and after heating, it was heated to reflux. temperature. After the temperature reached, 12 mmol of 1,1-carbonyldiimidazole (CDI) was added, and the reaction was stirred overnight, and the reaction solution was changed from a clear liquid to a yellow liquid. The reaction was cooled to rt. The organic layer was extracted with methylene chloride and water.
另外將3.2 mmol的(S,S)-1,2-二(1-萘基)-1,2-乙二醇((S,S)-1,2-Di(1-napthyl)-1,2-ethanediol)與dry THF(20 ml)置於反應瓶中，待其溶解後冰浴至0℃，於冰浴中緩慢加入氫化鈉(7.6 mmol)，持續攪拌反應10分鐘。In addition, 3.2 mmol of (S,S)-1,2-bis(1-naphthyl)-1,2-ethanediol ((S,S)-1,2-Di(1-napthyl)-1, 2-ethanediol) and dry THF (20 ml) were placed in a reaction flask, and after it was dissolved, it was ice-cooled to 0 ° C, and sodium hydride (7.6 mmol) was slowly added thereto in an ice bath, and the reaction was continuously stirred for 10 minutes.
隨後將先前取得的9.2 mmol酯類產物(a)加入，反應溫度由冰浴緩慢回復至室溫並持續攪拌反應1小時。反應結束後以減壓濃縮將THF去除得到黃色液體，使用二氯甲烷與水進行萃取，取有機層，加入無水硫酸鎂除水後，減壓濃縮得黃色初產物2.2 g。Subsequently, the previously obtained 9.2 mmol of the ester product (a) was added, and the reaction temperature was slowly returned from the ice bath to room temperature and the reaction was continuously stirred for 1 hour. After completion of the reaction, the THF was concentrated under reduced pressure to give EtOAc (EtOAc).
將黃色初產物以異丙醚與甲醇作再結晶，靜置一晚後以抽氣過濾得白色片狀結晶產物2.01g(2.4 mmol)，產率76.3%。The yellow primary product was recrystallized from isopropyl ether and methanol, and was allowed to stand for one night, and then filtered by suction to obtain 2.01 g (2.4 mmol) of white crystals.
利用上述反應式(II)可得到，a=1、b=0、c=1、m=1&Z=單鍵之下列化合物(b)Using the above reaction formula (II), the following compounds (b) with a=1, b=0, c=1, m=1&Z=single bond can be obtained.
實驗產物1：R=C5 H11 Experimental product 1: R = C 5 H 11
產率76.3%，Tm 167℃，1 H NMR(400 MHz,CDCl3 )確認：σ8.32(s,2H),7.99(d,J=8.0 Hz,4H),7.71(d,J=8.0 Hz,2H),7.63(d,J=8.1 Hz,2H),7.50(s,2H),7.45(s,2H),7.39(q,J=13.5,6.4 Hz,4H),7.22(q,J=16.6,7.9 Hz,6H),2.49(t,J=12.0 Hz,2H),1.86(d,J=9.3 Hz,8H),1.43(q,J=23.0,11.6 Hz,4H),1.32(t,J=6.03 Hz,8H),1.28(d,J=9.4 Hz,8H),1.25(s,2H),1.07(q,J=23.1,12.1 Hz,4H),0.90(t,J=6.7 Hz,6H).The yield was 76.3%, Tm 167 ° C, 1 H NMR (400 MHz, CDCl 3 ) confirmed: σ 8.32 (s, 2H), 7.99 (d, J = 8.0 Hz, 4H), 7.71 (d, J = 8.0 Hz , 2H), 7.63 (d, J = 8.1 Hz, 2H), 7.50 (s, 2H), 7.45 (s, 2H), 7.39 (q, J = 13.5, 6.4 Hz, 4H), 7.22 (q, J = 16.6, 7.9 Hz, 6H), 2.49 (t, J = 12.0 Hz, 2H), 1.86 (d, J = 9.3 Hz, 8H), 1.43 (q, J = 23.0, 11.6 Hz, 4H), 1.32 (t, J = 6.03 Hz, 8H), 1.28 (d, J = 9.4 Hz, 8H), 1.25 (s, 2H), 1.07 (q, J = 23.1, 12.1 Hz, 4H), 0.90 (t, J = 6.7 Hz, 6H).
以及實驗產物2：R=C7 H15 And experimental product 2: R = C 7 H 15
產率74.5%，Tm 153℃，1 H NMR(400 MHz,CDCl3 )確認：σ8.31(s,2H),7.98(d,J=8.2 Hz,4H),7.70(d,J=8.3 Hz,2H),7.63(d,J=8.2 Hz,2H),7.50(s,2H),7.44(s,2H),7.39(q,J=12.9,6.1 Hz,4H),7.22(q,J=16.4,8.0 Hz,6H),2.49(t,J=12.0 Hz,2H),1.86(d,J=9.6 Hz,8H),1.38(q,J=23.1,12.1 Hz,4H),1.28(s,22H),1.24(s,4H),1.04(q,J=23.0,10.8 Hz,4H),0.89(t,J=6.1 Hz,6H)。The yield was 74.5%, Tm 153 ° C, 1 H NMR (400 MHz, CDCl 3 ) confirmed: σ 8.31 (s, 2H), 7.98 (d, J = 8.2 Hz, 4H), 7.70 (d, J = 8.3 Hz) , 2H), 7.63 (d, J = 8.2 Hz, 2H), 7.50 (s, 2H), 7.44 (s, 2H), 7.39 (q, J = 12.9, 6.1 Hz, 4H), 7.22 (q, J = 16.4, 8.0 Hz, 6H), 2.49 (t, J = 12.0 Hz, 2H), 1.86 (d, J = 9.6 Hz, 8H), 1.38 (q, J = 23.1, 12.1 Hz, 4H), 1.28 (s, 22H), 1.24 (s, 4H), 1.04 (q, J = 23.0, 10.8 Hz, 4H), 0.89 (t, J = 6.1 Hz, 6H).
在下列實驗中，將比較以本發明之對掌性雙萘基旋光化合物摻雜至主動液晶組成配方，而與含常見摻雜物之液晶組成配方來進行比較。In the following experiments, the doping of the palmitic bis-naphthyl optically active compound of the present invention will be compared to an active liquid crystal composition, and compared with a liquid crystal composition containing a common dopant.
將實驗產物1-2添加到常見主動陣列液晶組成配方中，發現該摻雜的液晶組成物之VHR可保持≧90%，且實驗產物1-2具有HTP值≧40 μm-1 ，在相同波長條件下添加量較少(參見表1)。相較於已知的液晶摻雜物，本案之對掌性雙萘基旋光化合物可提供更好之功效，適合應用於不同液晶組成配方。The experimental product 1-2 was added to the common active array liquid crystal composition formula, and it was found that the VHR of the doped liquid crystal composition was maintained at ≧90%, and the experimental product 1-2 had an HTP value of ≧40 μm -1 at the same wavelength. The amount added is less under conditions (see Table 1). Compared with the known liquid crystal dopants, the palmitic bis-naphthyl optically active compound of the present invention can provide better efficacy and is suitable for application to different liquid crystal composition formulations.
＊未添加摻雜物前液晶物組成的VHR=100%，反射波長550 nm。主動陣列液晶組成物1&2之分子組成、比例不同，但皆為含氟的液晶配方。* The VHR of the liquid crystal composition before the addition of the dopant is 100%, and the reflection wavelength is 550 nm. The active array liquid crystal compositions 1 & 2 have different molecular compositions and ratios, but all are fluorine-containing liquid crystal formulations.
本發明之對掌性雙萘基旋光化合物添加到常見液晶組成配方中，使該摻雜的液晶組成物提供符合產業需求、良好的電壓維持率(VHR)。可使VHR保持≧90%，對於需要考慮VHR之主動陣列液晶顯示元件來說，特別可幫助提高其畫面對比與降低其影像殘留。且本發明之對掌性雙萘基旋光化合物具有較高的HTP值，在達到相同波長條件下使添加量減少，進而降低驅動電壓，影響液晶程度較小且成本更低。相較於已知的液晶摻雜物，本案之對掌性雙萘基旋光化合物確實更適合作為液晶摻雜物，應用於不同液晶組成配方。The palmitic bis-naphthyl optically active compound of the present invention is added to a common liquid crystal composition, so that the doped liquid crystal composition provides a good voltage maintenance ratio (VHR) in line with industrial demand. VHR can be kept at %90%, especially for active array liquid crystal display elements that need to consider VHR, especially to help improve their contrast and reduce image sticking. Moreover, the palm bis-naphthyl optically active compound of the present invention has a high HTP value, and the addition amount is reduced under the same wavelength condition, thereby lowering the driving voltage, affecting the liquid crystal level and lowering the cost. Compared with the known liquid crystal dopants, the palmitic bis-naphthyl optically active compound of the present invention is indeed more suitable as a liquid crystal dopant for different liquid crystal composition formulations.
將本發明所涵蓋一系列化合物之範例化合物列於下表2，但表2所示僅為不同a,b,c或m數值之範例，且或僅包括X、Y、Z、A1 、A2 或R各取代基之部分例子，而X、Y、Z、A1 、A2 或R所涵蓋之範圍如上述通式(I)所定義之。本發明所涵蓋一系列對掌性雙萘基旋光化合物並不限於表2所示的這些化合物。Exemplary compounds of a series of compounds encompassed by the present invention are listed in Table 2 below, but Table 2 shows only examples of different values of a, b, c or m, and or only X, Y, Z, A 1 , A Examples of some of the substituents of 2 or R, and the ranges covered by X, Y, Z, A 1 , A 2 or R are as defined in the above formula (I). The series of para-bis-naphthyl optically active compounds encompassed by the present invention are not limited to those compounds shown in Table 2.
實施例中以液晶組成配方來表示本發明所述對掌性雙萘基化合物之可能應用範圍與方式，但實際應用之領域或設計並不限於實施例或實驗所述之內容，而可轉用至其他相關領域、結構或產品，並為此領域發明者所能理解。In the embodiment, the liquid crystal composition formula is used to represent the possible application range and manner of the palmitic bis-naphthyl compound of the present invention, but the field or design of the practical application is not limited to the contents of the embodiment or the experiment, and can be used. To other related fields, structures or products, and to be understood by the inventors of this field.
雖然本發明已以實施例揭露如上，然其並非用以限定本發明，任何所屬技術領域中具有通常知識者，在不脫離本發明之精神和範圍內，當可作些許之更動與潤飾，故本發明之保護範圍當視後附之申請專利範圍所界定者為準。Although the present invention has been disclosed in the above embodiments, it is not intended to limit the invention, and any one of ordinary skill in the art can make some modifications and refinements without departing from the spirit and scope of the invention. The scope of the invention is defined by the scope of the appended claims.
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